I just came up with a cutesy little clue/answer that, if handled properly, could give a crossword puzzle solver a moment of consternation, and then, perhaps a chuckle.
It’s so simple, I’m too embarrassed to spell it out.
So if you have Mr. Shortz’s business email address, and it’s not too much trouble, I’d appreciate it if you’d please pass it along.
Check your email.
twicks, trying, very, very hard not to take it personally that you’d offer it to a perfect stranger rather than a fellow Doper… 
Yeah! twicks deserves first dibs! We’ve given her stuff before!
– Bob, still fondly remembering the glory 
I did end up giving it to Twicks, and not to Shortz…
Now, I’m a little regretful - but only because the clue/answer is kind of dumb.
Ah well…
Not dumb – just really, really hard – and very cool! I’ll write you an email a little later talking about cluing conventions, etc. Thanks very much for sending it to me – I can’t believe you thought I’d be too snobby to be bothered. Good lord, man, I hang out in MPSIMS – except when I’m starting Apprentice threads in Cafe Society.